HU194234B - Process for preparing substituted pyrido/1,2-c/imidazo /1,2-a/benzimidazoles and pharmaceuticals comprising the compounds - Google Patents

Process for preparing substituted pyrido/1,2-c/imidazo /1,2-a/benzimidazoles and pharmaceuticals comprising the compounds Download PDF

Info

Publication number: HU194234B
Authority: HU; Hungary
Prior art keywords: formula; benzimidazole; imidazo; hydrogen; compounds
Prior art date: 1983-09-15

Application number

HU843413A

Other languages

English (en)

Hungarian (hu)

Other versions

HUT36120A (en

Inventor

Volker Hitzel

Gerhard Rackur

Martin Bickel

Original Assignee

Hoechst Ag

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1983-09-15

Filing date

1984-09-10

Publication date

1988-01-28

1984-09-10 Application filed by Hoechst Ag filed Critical Hoechst Ag

1985-08-28 Publication of HUT36120A publication Critical patent/HUT36120A/hu

1988-01-28 Publication of HU194234B publication Critical patent/HU194234B/hu

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 62
238000004519 manufacturing process Methods 0.000 title claims description 4
239000003814 drug Substances 0.000 title description 8
150000001556 benzimidazoles Chemical class 0.000 title description 2
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 34
239000001257 hydrogen Substances 0.000 claims abstract description 34
-1 fuoryl Chemical class 0.000 claims abstract description 28
150000003839 salts Chemical class 0.000 claims abstract description 17
238000000034 method Methods 0.000 claims abstract description 15
238000002360 preparation method Methods 0.000 claims abstract description 15
150000002431 hydrogen Chemical class 0.000 claims abstract description 13
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 12
150000002367 halogens Chemical class 0.000 claims abstract description 11
229910052736 halogen Inorganic materials 0.000 claims abstract description 10
125000000217 alkyl group Chemical group 0.000 claims abstract description 9
125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 6
125000001589 carboacyl group Chemical group 0.000 claims abstract description 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 4
125000003342 alkenyl group Chemical group 0.000 claims abstract description 3
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract 2
125000003236 benzoyl group Chemical class [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract 2
239000002253 acid Substances 0.000 claims description 25
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
238000011282 treatment Methods 0.000 claims description 9
239000003960 organic solvent Substances 0.000 claims description 8
239000008194 pharmaceutical composition Substances 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 claims description 8
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
239000000546 pharmaceutical excipient Substances 0.000 claims description 6
125000004646 sulfenyl group Chemical group S(*)* 0.000 claims description 6
150000004820 halides Chemical class 0.000 claims description 5
125000004043 oxo group Chemical group O=* 0.000 claims description 4
239000000969 carrier Substances 0.000 claims description 3
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 3
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims description 3
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 3
125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 2
125000001797 benzyl group Chemical class [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
239000012442 inert solvent Substances 0.000 claims description 2
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
125000001475 halogen functional group Chemical group 0.000 claims 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
230000027119 gastric acid secretion Effects 0.000 abstract description 5
125000000304 alkynyl group Chemical group 0.000 abstract description 2
239000003112 inhibitor Substances 0.000 abstract description 2
239000000825 pharmaceutical preparation Substances 0.000 abstract description 2
XAKBSHICSHRJCL-UHFFFAOYSA-N [CH2]C(=O)C1=CC=CC=C1 Chemical class [CH2]C(=O)C1=CC=CC=C1 XAKBSHICSHRJCL-UHFFFAOYSA-N 0.000 abstract 1
125000000547 substituted alkyl group Chemical group 0.000 abstract 1
HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 33
IXPZYJRRDFZWHJ-UHFFFAOYSA-N 4h-imidazo[1,2-a]benzimidazole Chemical compound C1=CC=C2N3C=CN=C3NC2=C1 IXPZYJRRDFZWHJ-UHFFFAOYSA-N 0.000 description 26
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
239000000203 mixture Substances 0.000 description 12
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 11
239000002904 solvent Substances 0.000 description 11
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
239000000047 product Substances 0.000 description 10
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
125000004432 carbon atom Chemical group C* 0.000 description 7
239000000460 chlorine Substances 0.000 description 7
239000000243 solution Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
GWYGSVKDPUIQQA-UHFFFAOYSA-N 6,8,11-triazatetracyclo[10.4.0.01,6.07,11]hexadeca-2,4,7,9,12,14-hexaene Chemical class N12C=CC=CC22CC=CC=C2N2C1=NC=C2 GWYGSVKDPUIQQA-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 5
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
238000007363 ring formation reaction Methods 0.000 description 5
239000012279 sodium borohydride Substances 0.000 description 5
229910000033 sodium borohydride Inorganic materials 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 4
150000004987 o-phenylenediamines Chemical class 0.000 description 4
239000000725 suspension Substances 0.000 description 4
ITRSHHMEMKHFKV-UHFFFAOYSA-N 10-methylsulfanyl-6,8,11-triazatetracyclo[10.4.0.01,6.07,11]hexadeca-2,4,7,9,12,14-hexaene Chemical compound C1C=CC=C2N3C(SC)=CN=C3N3C12C=CC=C3 ITRSHHMEMKHFKV-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
238000009835 boiling Methods 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
229960001701 chloroform Drugs 0.000 description 3
238000004440 column chromatography Methods 0.000 description 3
239000013078 crystal Substances 0.000 description 3
201000010099 disease Diseases 0.000 description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
229940079593 drug Drugs 0.000 description 3
230000002496 gastric effect Effects 0.000 description 3
230000002265 prevention Effects 0.000 description 3
230000008707 rearrangement Effects 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
239000000126 substance Substances 0.000 description 3
229910052717 sulfur Inorganic materials 0.000 description 3
239000011593 sulfur Substances 0.000 description 3
239000003826 tablet Substances 0.000 description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 2
DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical class NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 2
OKXUGIDLQRUMFH-UHFFFAOYSA-N 6,8,11-triazatetracyclo[10.4.0.01,6.07,11]hexadeca-2,4,7,9,12,14-hexaene-10-thiol Chemical compound C1C=CC=C2N3C(S)=CN=C3N3C12C=CC=C3 OKXUGIDLQRUMFH-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 2
208000018522 Gastrointestinal disease Diseases 0.000 description 2
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
239000007868 Raney catalyst Substances 0.000 description 2
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
229910000564 Raney nickel Inorganic materials 0.000 description 2
XNNYUWOXNUAPOA-UHFFFAOYSA-N S-(6,8,11-triazatetracyclo[10.4.0.01,6.07,11]hexadeca-2,4,7,9,12,14-hexaen-10-yl) benzenecarbothioate Chemical compound C=1N=C2N3C=CC=CC33CC=CC=C3N2C=1SC(=O)C1=CC=CC=C1 XNNYUWOXNUAPOA-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
208000025865 Ulcer Diseases 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
230000001476 alcoholic effect Effects 0.000 description 2
229940069428 antacid Drugs 0.000 description 2
239000003159 antacid agent Substances 0.000 description 2
125000005605 benzo group Chemical group 0.000 description 2
239000002775 capsule Substances 0.000 description 2
239000004202 carbamide Substances 0.000 description 2
125000004093 cyano group Chemical group *C#N 0.000 description 2
239000008298 dragée Substances 0.000 description 2
239000003995 emulsifying agent Substances 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
210000001035 gastrointestinal tract Anatomy 0.000 description 2
239000008103 glucose Substances 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
150000004678 hydrides Chemical class 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
238000002955 isolation Methods 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
239000003921 oil Substances 0.000 description 2
235000019198 oils Nutrition 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
230000001681 protective effect Effects 0.000 description 2
238000000746 purification Methods 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
150000003573 thiols Chemical class 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
125000005490 tosylate group Chemical group 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
231100000397 ulcer Toxicity 0.000 description 2
XHESWTYIIAQOSS-UHFFFAOYSA-N 10-(ethoxymethylsulfanyl)-6,8,11-triazatetracyclo[10.4.0.01,6.07,11]hexadeca-2,4,7,9,12,14-hexaene Chemical compound C1C=CC=C2N3C(SCOCC)=CN=C3N3C12C=CC=C3 XHESWTYIIAQOSS-UHFFFAOYSA-N 0.000 description 1
HHBJIQJIBPCLAS-UHFFFAOYSA-N 10-benzhydrylsulfanyl-14-methoxy-13,15-dimethyl-5-(trifluoromethyl)-6,8,11-triazatetracyclo[10.4.0.01,6.07,11]hexadeca-2,4,7,9,12,14-hexaene Chemical compound N12C3=C(C)C(OC)=C(C)CC43C=CC=C(C(F)(F)F)N4C2=NC=C1SC(C=1C=CC=CC=1)C1=CC=CC=C1 HHBJIQJIBPCLAS-UHFFFAOYSA-N 0.000 description 1
BGIHYCGFLJPQIG-UHFFFAOYSA-N 10-benzylsulfanyl-14-methoxy-13,15-dimethyl-5-(trifluoromethyl)-6,8,11-triazatetracyclo[10.4.0.01,6.07,11]hexadeca-2,4,7,9,12,14-hexaene Chemical compound N12C3=C(C)C(OC)=C(C)CC43C=CC=C(C(F)(F)F)N4C2=NC=C1SCC1=CC=CC=C1 BGIHYCGFLJPQIG-UHFFFAOYSA-N 0.000 description 1
YHNNMDWVTSYLLT-UHFFFAOYSA-N 10-benzylsulfanyl-6,8,11-triazatetracyclo[10.4.0.01,6.07,11]hexadeca-2,4,7,9,12,14-hexaene Chemical compound C=1N=C2N3C=CC=CC33CC=CC=C3N2C=1SCC1=CC=CC=C1 YHNNMDWVTSYLLT-UHFFFAOYSA-N 0.000 description 1
HSFQXCQQPPKEMC-UHFFFAOYSA-N 10-ethylsulfanyl-6,8,11-triazatetracyclo[10.4.0.01,6.07,11]hexadeca-2,4,7,9,12,14-hexaene Chemical compound C1C=CC=C2N3C(SCC)=CN=C3N3C12C=CC=C3 HSFQXCQQPPKEMC-UHFFFAOYSA-N 0.000 description 1
NMQLKXRDZYBFON-UHFFFAOYSA-N 10-propylsulfanyl-6,8,11-triazatetracyclo[10.4.0.01,6.07,11]hexadeca-2,4,7,9,12,14-hexaene Chemical compound C1C=CC=C2N3C(SCCC)=CN=C3N3C12C=CC=C3 NMQLKXRDZYBFON-UHFFFAOYSA-N 0.000 description 1
OOQPHCPZNYCLJY-UHFFFAOYSA-N 10-tert-butylsulfanyl-6,8,11-triazatetracyclo[10.4.0.01,6.07,11]hexadeca-2,4,7,9,12,14-hexaene Chemical compound C1C=CC=C2N3C(SC(C)(C)C)=CN=C3N3C12C=CC=C3 OOQPHCPZNYCLJY-UHFFFAOYSA-N 0.000 description 1
CCHDZAAVFHGUIY-UHFFFAOYSA-N 14-methoxy-10-(methoxymethylsulfanyl)-13,15-dimethyl-5-(trifluoromethyl)-6,8,11-triazatetracyclo[10.4.0.01,6.07,11]hexadeca-2,4,7,9,12,14-hexaene Chemical compound C1C(C)=C(OC)C(C)=C2N3C(SCOC)=CN=C3N3C12C=CC=C3C(F)(F)F CCHDZAAVFHGUIY-UHFFFAOYSA-N 0.000 description 1
BTFSEDAKFPBTOG-UHFFFAOYSA-N 14-methoxy-13,15-dimethyl-10-propylsulfanyl-5-(trifluoromethyl)-6,8,11-triazatetracyclo[10.4.0.01,6.07,11]hexadeca-2,4,7,9,12,14-hexaene Chemical compound C1C(C)=C(OC)C(C)=C2N3C(SCCC)=CN=C3N3C12C=CC=C3C(F)(F)F BTFSEDAKFPBTOG-UHFFFAOYSA-N 0.000 description 1
FTFSMIABGWFRNI-UHFFFAOYSA-N 14-methoxy-13,15-dimethyl-5-(trifluoromethyl)-6,8,11-triazatetracyclo[10.4.0.01,6.07,11]hexadeca-2,4,7,9,12,14-hexaene-10-thiol Chemical compound C1=CC=C(C(F)(F)F)N2C3=NC=C(S)N3C3=C(C)C(OC)=C(C)CC231 FTFSMIABGWFRNI-UHFFFAOYSA-N 0.000 description 1
CLWJNBCCRWKBGS-UHFFFAOYSA-N 14-methoxy-13,15-dimethyl-6,8,11-triazatetracyclo[10.4.0.01,6.07,11]hexadeca-2,4,7,9,12,14-hexaene 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC=CN2C3=NC=CN3C3=C(C)C(OC)=C(C)CC231 CLWJNBCCRWKBGS-UHFFFAOYSA-N 0.000 description 1
YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
JPMRGPPMXHGKRO-UHFFFAOYSA-N 2-(chloromethyl)pyridine hydrochloride Chemical compound Cl.ClCC1=CC=CC=N1 JPMRGPPMXHGKRO-UHFFFAOYSA-N 0.000 description 1
HBDKFZNDMVLSHM-UHFFFAOYSA-N 2-(pyridin-2-ylmethylsulfinyl)-1h-benzimidazole Chemical compound N=1C2=CC=CC=C2NC=1S(=O)CC1=CC=CC=N1 HBDKFZNDMVLSHM-UHFFFAOYSA-N 0.000 description 1
BLQBFXLELLMDJN-UHFFFAOYSA-N 2-chloro-1-(pyridin-2-ylmethyl)benzimidazole Chemical compound ClC1=NC2=CC=CC=C2N1CC1=CC=CC=N1 BLQBFXLELLMDJN-UHFFFAOYSA-N 0.000 description 1
AYPSHJCKSDNETA-UHFFFAOYSA-N 2-chloro-1h-benzimidazole Chemical compound C1=CC=C2NC(Cl)=NC2=C1 AYPSHJCKSDNETA-UHFFFAOYSA-N 0.000 description 1
CSDSSGBPEUDDEE-UHFFFAOYSA-N 2-formylpyridine Chemical compound O=CC1=CC=CC=N1 CSDSSGBPEUDDEE-UHFFFAOYSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
HDECRAPHCDXMIJ-UHFFFAOYSA-N 2-methylbenzenesulfonyl chloride Chemical compound CC1=CC=CC=C1S(Cl)(=O)=O HDECRAPHCDXMIJ-UHFFFAOYSA-N 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
IUNGQUVZQMMCAA-UHFFFAOYSA-N 3-(pyridin-2-ylmethyl)-1h-benzimidazol-2-one Chemical compound O=C1NC2=CC=CC=C2N1CC1=CC=CC=N1 IUNGQUVZQMMCAA-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
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XCVDWUYVCFZVTD-UHFFFAOYSA-N S-(5-tert-butyl-6,8,11-triazatetracyclo[10.4.0.01,6.07,11]hexadeca-2,4,7,9,12,14-hexaen-10-yl) ethanethioate Chemical compound C1C=CC=C2N3C(SC(=O)C)=CN=C3N3C12C=CC=C3C(C)(C)C XCVDWUYVCFZVTD-UHFFFAOYSA-N 0.000 description 1
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BAULBIKKBYYFNN-UHFFFAOYSA-N S-[14-methoxy-13,15-dimethyl-5-(trifluoromethyl)-6,8,11-triazatetracyclo[10.4.0.01,6.07,11]hexadeca-2,4,7,9,12,14-hexaen-10-yl] benzenecarbothioate Chemical compound N12C3=C(C)C(OC)=C(C)CC43C=CC=C(C(F)(F)F)N4C2=NC=C1SC(=O)C1=CC=CC=C1 BAULBIKKBYYFNN-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/53—Nitrogen atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Steroid Compounds (AREA)

HU843413A 1983-09-15 1984-09-10 Process for preparing substituted pyrido/1,2-c/imidazo /1,2-a/benzimidazoles and pharmaceuticals comprising the compounds HU194234B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19833333314 DE3333314A1 (de)	1983-09-15	1983-09-15	Substituierte pyrido(1,2-c)imidazo(1,2-a)benzimidazole, verfahren zu ihrer herstellung, ihre verwendung sowie pharmazeutische praeparate auf basis dieser verbindungen

Publications (2)

Publication Number	Publication Date
HUT36120A HUT36120A (en)	1985-08-28
HU194234B true HU194234B (en)	1988-01-28

Family

ID=6209147

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HU843413A HU194234B (en)	1983-09-15	1984-09-10	Process for preparing substituted pyrido/1,2-c/imidazo /1,2-a/benzimidazoles and pharmaceuticals comprising the compounds

Country Status (14)

Country	Link
US (1)	US4585775A (da)
EP (1)	EP0138034B1 (da)
JP (1)	JPS6084289A (da)
KR (1)	KR850002100A (da)
AT (1)	ATE41775T1 (da)
AU (1)	AU3306884A (da)
CA (1)	CA1247621A (da)
DE (2)	DE3333314A1 (da)
DK (1)	DK440084A (da)
ES (2)	ES535875A0 (da)
GR (1)	GR80358B (da)
HU (1)	HU194234B (da)
PT (1)	PT79200B (da)
ZA (1)	ZA847261B (da)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AR243167A1 (es)	1985-08-24	1993-07-30	Hoechst Ag	Procedimiento para la preparacion de toluidinas sustituidas.
DE3639926A1 (de) *	1986-11-22	1988-06-01	Hoechst Ag	Substituierte thienoimidazoltoluidin-derivate, verfahren zu ihrer herstellung, sie enthaltende pharmazeutische zubereitungen und ihre verwendung als magensaeuresekretionshemmer
US5008282A (en) *	1988-12-28	1991-04-16	Kotobuki Seiyaku Co. Ltd.	Cyclic guanidine derivatives, anti-ulceratives and methods of manufacturing the same
SE9500051D0 (sv) *	1995-01-09	1995-01-09	Frode Rise	Antioxidants, tissue- and/or neuroprotectants
RU2645917C1 (ru) *	2017-04-12	2018-03-01	Федеральное государственное бюджетное образовательное учреждение высшего образования "Ярославский государственный университет им. П.Г. Демидова"	Способ синтеза пиридо[1,2-а]имидазо[4,5-f]бензимидазола и его производных

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS4821274Y1 (da) *	1969-05-31	1973-06-20
JPS5124517B1 (da) *	1971-03-15	1976-07-24
US3880866A (en) *	1972-05-01	1975-04-29	American Home Prod	7-Azaindole fused heterocyclic compounds
US3880870A (en) *	1973-04-18	1975-04-29	American Home Prod	7-Azaindole fused heterocyclic compounds
US3911130A (en) *	1973-04-18	1975-10-07	American Home Prod	Novel 7-azaindole fused heterocyclic compounds for producing analgesia
SE416649B (sv) *	1974-05-16	1981-01-26	Haessle Ab	Forfarande for framstellning av foreningar som paverkar magsyrasekretionen
SE7804231L (sv) *	1978-04-14	1979-10-15	Haessle Ab	Magsyrasekretionsmedel
GB2028317B (en) *	1978-08-15	1982-11-10	Pfizer Ltd	2-(imidazol-1-ylmethyl)-pyridine and -quinoline thromboxane synthetase inhibitors
US4255573A (en) *	1979-03-29	1981-03-10	Adhikary Parimal K	Imidazoindole derivatives and pharmaceutical compositions comprising imidazoindole derivatives
JPS56116980A (en) *	1980-02-15	1981-09-14	Nippon Bulge Ind	Bend for pipings
US4254127A (en) *	1980-04-03	1981-03-03	Janssen Pharmaceutica, N.V.	1,3-Dihydro-1-[(1-piperidinyl)alkyl]-2H-benzimidazol-2-one derivatives
US4472409A (en) *	1981-11-05	1984-09-18	Byk Gulden Lomberg Chemische Fabrik Gesellschaft Mit Beschrankter Haftung	2-Pyridylmethyl thio(sulfinyl)benzimidazoles with gastric acid secretion inhibiting effects

1983
- 1983-09-15 DE DE19833333314 patent/DE3333314A1/de not_active Withdrawn
1984
- 1984-09-06 EP EP84110589A patent/EP0138034B1/de not_active Expired
- 1984-09-06 DE DE8484110589T patent/DE3477490D1/de not_active Expired
- 1984-09-06 AT AT84110589T patent/ATE41775T1/de not_active IP Right Cessation
- 1984-09-10 HU HU843413A patent/HU194234B/hu not_active IP Right Cessation
- 1984-09-13 US US06/650,106 patent/US4585775A/en not_active Expired - Fee Related
- 1984-09-13 GR GR80358A patent/GR80358B/el unknown
- 1984-09-13 CA CA000463077A patent/CA1247621A/en not_active Expired
- 1984-09-13 ES ES535875A patent/ES535875A0/es active Granted
- 1984-09-14 ZA ZA847261A patent/ZA847261B/xx unknown
- 1984-09-14 AU AU33068/84A patent/AU3306884A/en not_active Abandoned
- 1984-09-14 KR KR1019840005595A patent/KR850002100A/ko not_active Ceased
- 1984-09-14 PT PT79200A patent/PT79200B/pt unknown
- 1984-09-14 DK DK440084A patent/DK440084A/da not_active Application Discontinuation
- 1984-09-14 JP JP59191867A patent/JPS6084289A/ja active Pending
1985
- 1985-02-19 ES ES540511A patent/ES8602790A1/es not_active Expired

Also Published As

Publication number	Publication date
GR80358B (en)	1985-01-11
ZA847261B (en)	1985-05-29
ATE41775T1 (de)	1989-04-15
JPS6084289A (ja)	1985-05-13
CA1247621A (en)	1988-12-28
AU3306884A (en)	1985-03-21
KR850002100A (ko)	1985-05-06
PT79200B (de)	1986-09-10
HUT36120A (en)	1985-08-28
PT79200A (de)	1984-10-01
US4585775A (en)	1986-04-29
DE3333314A1 (de)	1985-03-28
EP0138034B1 (de)	1989-03-29
ES540511A0 (es)	1985-12-01
ES8505678A1 (es)	1985-06-01
DK440084D0 (da)	1984-09-14
ES8602790A1 (es)	1985-12-01
ES535875A0 (es)	1985-06-01
EP0138034A1 (de)	1985-04-24
DK440084A (da)	1985-03-16
DE3477490D1 (en)	1989-05-03

Legal Events

Date	Code	Title	Description
1990-06-28	HU90	Patent valid on 900628
1991-08-28	HMM4	Cancellation of final prot. due to non-payment of fee

Publication	Publication Date	Title
US7714009B2 (en)	2010-05-11	Nitrogen-containing fused heterocyclic compounds
US4696931A (en)	1987-09-29	Imidazole derivatives and pharmaceutical compositions containing them
EP0859778B1 (en)	2001-12-19	TETRAHYDROIMIDAZOPYRIDOINDOLEDIONES AS INHIBITORS OF cGMP SPECIFIC PDE
PL175932B1 (pl)	1999-03-31	Nowe imidazopirydyny, sposób wytwarzania nowych imidazopirydyn i środek leczniczy zawierający nowe imidazopirydyny
US4820710A (en)	1989-04-11	Benzimidazole derivatives and pharmaceutical compositions containing them
US4556653A (en)	1985-12-03	Pyrido[1,5]benzodiazepinone derivatives and pharmacological activities thereof
SK285165B6 (sk)	2006-07-07	Tetrahydropyridoétery, farmaceutický prostriedok s ich obsahom a ich použitie
CZ99797A3 (en)	1997-09-17	Purine and guanine compounds as pnp inhibitors
HU197330B (en)	1989-03-28	Process for preparing thienoimidazole derivatives and pharmaceuticals comprising the same
EP0104522B1 (en)	1991-05-29	New pyrazolo(3,4-b)pyridine derivatives and process for producing them
KR900003368B1 (ko)	1990-05-16	신규한 인데노티아졸 유도체의 제조방법
IE911406A1 (en)	1991-11-06	New pyridazines
KR940005020B1 (ko)	1994-06-09	톨루이딘 유도체의 제조방법
KR910005854B1 (ko)	1991-08-05	헤테로사이클릭 그룹을 함유하는 이미다조 퀴놀린 유도체의 제조방법
US4585775A (en)	1986-04-29	Substituted pyrido (1,2-c)imidazo(1,2-a)benzimidazoles, processes for their preparation, their use and pharmaceutical preparations based on these compounds
US4209620A (en)	1980-06-24	Substituted 3-(1H-tetrazol-5-yl)-4H-pyrido[1,2-a]pyrimidin-4-one derivatives having antiallergy activity
CN101142208B (zh)	2012-05-23	作为呼吸道合胞病毒复制抑制剂的1,3-二氢-苯并咪唑-2-亚基胺
US4479948A (en)	1984-10-30	Triazino(2,1-a)isoquinoline derivatives, compositions and their use as medicaments
US4720496A (en)	1988-01-19	Pyridotriazoloquinazolines and triazolopyridoquinazolines useful as antiallergics
US5008282A (en)	1991-04-16	Cyclic guanidine derivatives, anti-ulceratives and methods of manufacturing the same
US5240944A (en)	1993-08-31	Cyclic guanidine derivatives, anti-ulceratives and method of manufacturing the same
US4666900A (en)	1987-05-19	Anti-ulcer and anti-hypersecretion dibenzoimidazothiazepine derivatives, compositions, and method of use therefor
RU2033414C1 (ru)	1995-04-20	Производные 4,5,6,7-тетрагидробензимидазола
US4483858A (en)	1984-11-20	8-[2-Imidazolylmethyloxy(thio, or amino)]-imidazo[1,2-a]pyrazines and derivatives for treating hypertension
US4703044A (en)	1987-10-27	Imidazoquinolines containing other heterocyclic groups, useful as anti-ulcer or anti-secretory agents